Comb-like polyetheralkanolamines in inks and coatings

ABSTRACT

Provided herein are compositions useful as ink or coatings which contain novel dispersants that are capable of dispersing pigments which are traditionally difficult to disperse while maintaining acceptable levels of viscosity. Use of dispersants as taught herein enables the preparation of a wide variety of inks and coatings having high pigment loading and existing within a conventionally-useful viscosity range.

CROSS-REFERENCE TO RELATED APPLICATIONS

This Application is a continuation in part of international applicationnumber PCT/US05/008126 filed Mar. 10, 2005, which claimed priority toU.S. Provisional Application Ser. No. 60/570,600 filed May 13, 2004.

FIELD OF THE INVENTION

The present invention relates to a non-aqueous and aqueous pigmentedinks and coatings, wherein the pigment dispersant is apolyetheralkanolamine comb polymer, and method of making the same. Thisinvention also relates to aqueous pigmented inks which can be used inink jet printers and pigmented coatings.

BACKGROUND INFORMATION

When a pigment is used as a colorant, an ink composition is prepared bymixing the concentrated pigment dispersion which contains pigment,water, dispersant and the like with water, resin, a water-solubleorganic medium, and other ingredients. U.S. Pat. No. 6,818,053 disclosesa production process for producing a pigment dispersion comprising thesteps of (a) providing a mixture consisting essentially of a pigment, adispersant, a polysiloxane surfactant and/or an alkanediol, a polyhydricalcohol and water; and (b) dispersing the mixture to produce the pigmentdispersion. The patent also claims an ink composition prepared from theabove pigment dispersion.

In pigmented ink compositions, the pigment dispersion is generallystabilized by a dispersant which serves to prevent the pigment particlesfrom agglomerating and settling out of the carrier. U.S. Pat. No.5,085,698 discloses an ink composition comprising pigment, aqueousmedium, and an acrylic/acrylate block copolymer as a stabilizing agent.U.S. Pat. No. 5,589,522 employs a graft polymer comprising a hydrophilicpolyacrylic acid backbone and hydrophobic segment side chains in anaqueous ink composition. U.S. Pat. No. 4,597,794 discloses an aqueousink dispersion for ink jet printers in which pigment is contained in apolymer having ionic hydrophilic segments and aromatic hydrophobicsegments that adhere to the pigment surface.

U.S. Pat. No. 5,948,843 relates to a lithographic printing inkcontaining a dispersing agent of a reaction product of a styrene/maleicanhydride (SMA) copolymer and an alcohol as a pigment dispersant. U.S.Pat. No. 5,302,197 employs hydroxyl-terminated branched polymer off ashort carbon chain in an ink jet ink.

While prior pigmented ink compositions showed acceptable stability forthe pigment dispersion, improved pigment ink dispersion is still neededto further lower the ink viscosity, impart better print density,increase pigment loading, and lower degree of shear thinning afteraging. It is therefore an object of the present invention to provide animproved pigmented ink composition.

Additionally, pigments may be incorporated into pigmented coatingcompositions by mixing a pigment dispersion and a grind resin. Thecoating composition may further include additives such as crosslinkers,solvents, additional polymer resins, flow and appearance control agents,fillers, and the like.

In general, the coating compositions may be used to provide a protectivelayer, which is ascetically pleasing, on metals, alloys, composites,plastics, concrete, cast iron, wood, ceramic, paper, film, foil, vinyl,textile, glass, leather, and the like materials. In particular, thecoating compositions disclosed herein may be applied to the surfaces ofautomobiles, automobile parts, decks, fences, homes, and the likesurfaces.

U.S. Pat. No. 7,005,473 discloses a pigment dispersion used insolventborne coating compositions. The patent further discloses the useof a polymeric pigment disperant as the grind resin to incorporate thepigment into the pigment dispersion for solventborne coatingcompositions. U.S. Pat. No. 7,005,473 is hereby incorporated byreference in full, to the extent that its disclosure does not contradictthe instant disclosure.

While prior pigmented coating compositions showed acceptable stabilityfor the pigment dispersion, improved pigment dispersion is still neededto further lower the coating viscosity, impart better print density,increase pigment loading, and lower degree of shear thinning afteraging. It is therefore an object of the present invention to provide animproved pigmented coating composition.

The present invention thus defines a novel and inventive class ofdispersant materials useful in formulating inks, coatings, and the like,including ink formulations and pigmented coating compositions comprisingsuch dispersant materials as defined herein.

SUMMARY OF THE INVENTION DEFINITIONS

As used herein, the term “reaction” or “reacting” mean combining morethan one reactant, or combining one or more reactant in the presence ofan initiator and/or a catalyst.

As used herein, the term “dispersant” means a comb polymer. Suitablecomb polymers and methods of making the same are disclosed below herein.

As used herein, the term “pigmented dispersion” means a mixture of thedispersant and a suitable pigment. Suitable pigments are disclosed belowherein.

As used herein, the term “hydrocarbyl”, when referring to a substituentor group is used in its ordinary sense. Specifically, it refers to agroup having a carbon atom directly attached to the remainder of themolecule and having predominantly hydrocarbon character. Examples ofhydrocarbyl substituents or groups include: (1) hydrocarbon (includinge.g., alkyl, alkenyl, alkynyl) substituents, alicyclic (including e.g.,cycloalkyl, cycloalkenyl) substituents, and aromatic-, aliphatic-, andalicyclic-substituted aromatic substituents, as well as cyclicsubstituents wherein the ring is completed through another portion ofthe molecule (e.g., two substituents together form an alicyclicradical); (2) substituted hydrocarbon substituents, that is,substituents containing non-hydrocarbon groups which, in the context ofthis invention, do not alter the predominantly hydrocarbon substituent(e.g., halo (especially chloro and fluoro), hydroxy, alkoxy, mercapto,alkylmercapto, nitro, nitroso, and sulfoxy); (3) hetero substituents,that is, substituents which, while having a predominantly hydrocarboncharacter, in the context of this invention, contain other than carbonin a ring or chain otherwise composed of carbon atoms. Heteroatomsinclude sulfur, oxygen, nitrogen, and encompass substituents as pyridyl,furyl, thienyl and imidazolyl. In general, no more than two, preferablyno more than one, non-hydrocarbon substituent will be present for everyten carbon atoms in the hydrocarbyl group; typically, there will be nonon-hydrocarbon substituents in the hydrocarbyl group.)

For the purposes of this application, the weight average molecularweight is given by:

$M_{w} = \frac{\sum\limits_{i}{n_{i}M_{i}^{2}}}{\sum\limits_{i}{n_{i}M_{i}}}$

where n_(i) is the number fraction of molecules of molecular weightM_(i).

-   The number average molecular weight is given by:

$M_{n} = \frac{\sum\limits_{i}{n_{i}M_{i}}}{\sum\limits_{i}n_{i}}$

where n_(i) is the number fraction of molecules of molecular weightM_(i). M_(w), and M_(n) are typically determined by Gel PermeationChromatography as disclosed in Macromolecules, Vol. 34 Number 19, Page6812 (2001).

For purpose of this invention and the claims thereto, viscosity wasmeasured using a Brookfield Viscometer; Tint Strength (Sherwin WilliamsSuperpaint Flat Interior

Latex Extra White to dispersion, 50 parts to 0.50 partsrespectively)—mixed on a Hauschild mixer for 1 minute at 1800 rpm.Drawdowns of the tint mixture versus standard were made on Leneta 3NT-4regular bond stock using a #20 wire wound rod; color, transparency, andgloss was determined by testing prints made with 360P 113 anilox onLeneta 3NT-3, film, and foil. Further all percentages are by weight andall molecular weights are M_(w), unless otherwise noted or indicated bythe context.

The present invention provides ink or coating compositions whichcomprise:

-   a) a pigment component; and b) an effective pigment-dispersing    amount of a dispersant having the structure:

in which R₁ may be any C₁-C₁₀₀ aliphatic hydrocarbyl group; R₂ may beany alkoxylated hydrocarbyl group defined by the structure:

in which R₃ is selected from the group consisting of: hydrogen, and anyC₁ to about C₂₄ hydrocarbyl group; X₁, X₂, X₃, X₄, X₅, and X₆ in eachoccurrence are independently selected from the group consisting of:hydrogen, methyl and ethyl, subject to the proviso that at least one ofthe two X groups that are attached to the same alkoxy unit are hydrogen,p, q, and r may each independently be any integer between zero and about100, including zero, subject to the proviso that at least one of p, q,and r is not zero; n is any integer between 1 and about 50; and s may beeither 0 or 1.

-   In another embodiment, this invention relates to:-   1) A composition comprising:

a) a pigment component; and

-   b) an effective pigment-dispersing amount of a dispersant having the    structure:

in which R₁ may be any C₁-C₁₀₀ aliphatic hydrocarbyl group; R₂ may beany alkoxylated hydrocarbyl group defined by the structure:

in which R₃ is selected from the group consisting of: hydrogen, and anyC₁ to about C₂₄ hydrocarbyl group; X₁, X₂, X₃, X₄, X₅, and X₆ in eachoccurrence are independently selected from the group consisting of:hydrogen, methyl and ethyl, subject to the proviso that at least one ofthe two X groups that are attached to the same alkoxy unit are hydrogen,p, q, and r may each independently be any integer between zero and about100, including zero, subject to the proviso that at least one of p, q,and r is not zero; n is any integer between 1 and about 50; and s may beeither 0 or 1.

-   2) The composition according to paragraph 1, wherein the pigment    component is selected from the group consisting of phthalocyanine,    carbon black, titanium oxides, chromates, sulfides, iron oxides, azo    lakes, insoluble azo pigment, condensed azo pigments, chelate azo    pigments, monoazo pigments, monoarylide, B-naphthol, naphthol AS,    benzimidazolone, metal precipitated azo, disazo pigments, diarylide,    disazo condensation, diazopyrazoione, bisacetoacetarylide,    phthalocyanine pigments, perylenes, perylene, perinone pigments,    anthraquinone pigments, quinacridone pigments, dioxazine pigments,    thioindigo pigments, isoindolinone pigments, quinophthalone    pigments, base dye lakes, acid dye lakes, nitro pigments, nitroso    pigments, aniline black daylight fluorescent pigments, graphite    carbon, isoindoline, isoindolinon, indigoid, diketopyrrolopyrrole,    triarylcarbonium, metal complexes, pearl, liquid crystal pigments,    fluorescence, and functional derivatives of the above-mentioned    pigments.-   3) The composition according to paragraphs 1 or 2, further    comprising a solvent.-   4) The composition according to paragraph 3, wherein said solvent    comprises one or more organic solvents selected from the group    consisting of: polyhydric alcohols; glycols; diols; glycol esters;    glycol ethers; polyalkyl glycols; lower alkyl ethers of polyhydric    alcohols; alcohols having fewer than about 8 carbon atoms per    molecule; ketones; ethers; esters; and lactams.-   5) The composition according to paragraph 3, wherein the solvent    comprises water.-   6) The composition of paragraph 3, wherein the solvent is selected    from the group consisting of water; hexane; mineral spirits;    toluene; soy bean oil; castor oil; tall oil fatty acids; polyhydric    alcohols; glycols; diols; glycol esters; glycol ethers; polyalkyl    glycols; lower alkyl ethers of polyhydric alcohols; alcohols having    fewer than about 8 carbon atoms per molecule; ketones; ethers;    esters; lactams, ethylene glycol, propylene glycol; butanediol;    pentanediol; glycerol; propylene glycol laurate; polyethylene    glycol; ethylene glycol monomethyl ether, ethylene glycol mono-ethyl    ether; ethylene glycol mono-butyl ether; alcohols having fewer than    about 8 carbon atoms per molecule such as methanol, ethanol,    propanol, iso-propanol; acetone; dioxane; ethyl acetate, propyl    acetate, tertiary-butyl acetate, and 2-pyrrolidone.-   7) The composition of paragraphs 3-6, wherein the amount of said    solvent component present is any amount between about 10% and 99% by    weight based on the total weight of said composition.-   8) The composition of paragraphs 3-7, wherein the amount of said    solvent component present is any amount between about 50% and 99% by    weight based on the total weight of said composition.-   9) The composition of paragraphs 1-8, wherein the composition    comprises from about 1 weight % to about 80 weight % pigment, based    on the total weight of the composition.-   10) The composition of paragraphs 1-9, wherein the composition    comprises from about 1 weight % to about 40 weight % pigment, based    on the total weight of the composition.-   11) The composition of paragraphs 1-10, wherein the composition    comprises from about 2 weight % to about 10 weight % pigment, based    on the total weight of the composition.-   12) The use of the dispersant as described in paragraphs 1-12 in an    ink composition or a coating composition.-   13) A dispersion comprising water, a pigment, and the dispersant as    described in paragraph 1.-   14) A dispersion comprising an organic solvent according to any    foregoing claim, a pigment, and a dispersant as described in    paragraph 1.-   15) A composition according to paragraphs 1-14, wherein said pigment    comprises any pigment as stated in any foregoing claim.-   16) The use of a dispersant within the scope of the limitations    specified for the dispersant component of a composition according to    paragraphs 1-15, in an ink or coating which is either applied to or    intended to be applied to a substrate which comprises a material    selected from the group consisting of cellulose, any olefin polymer,    glass, polyester, polyvinylchloride, polyamides, polyurethane, metal    composites, and the like.-   17) Any liquid ink composition which comprises a material falling    within the definition of the dispersant component of the composition    specified in paragraphs 1-16.-   18) An article comprising an ink or a coating,

wherein the ink further comprises:

-   -   a) a pigment component; and    -   b) an effective pigment-dispersing amount of a dispersant having        the structure:

-   -    in which R₁ may be any C₁-C₁₀₀ aliphatic hydrocarbyl group; R₂        may be any alkoxylated hydrocarbyl group defined by the        structure:

in which R₃ is selected from the group consisting of: hydrogen, and anyC₁ to about C₂₄ hydrocarbyl group; X₁, X₂, X₃, X₄, X₅, and X₆ in eachoccurrence are independently selected from the group consisting of:hydrogen, methyl and ethyl, subject to the proviso that at least one ofthe two X groups that are attached to the same alkoxy unit are hydrogen,p, q, and r may each independently be any integer between zero and about100, including zero, subject to the proviso that at least one of p, q,and r is not zero; n is any integer between 1 and about 50; and s may beeither 0 or 1.

-   19) The article of paragraph 18, wherein the article is formed from    a material selected from the group consisting of metals, alloys,    composites, plastics, concrete, cast iron, wood, ceramic, paper,    film, foil, vinyl, textile, glass, and leather.-   20) A process for the formation of an ink or coating composition    comprising:    -   a) reacting a monofunctional amine-terminated polyether and a        glycidyl ether of a polyol to form a dispersant; and    -   b) contacting the dispersant and a pigment to form a pigment        dispersion.-   21) The process of paragraph 20, wherein the glycidyl ether of the    polyol comprises aromatic epoxide groups, and wherein 20 to 90    percent of the aromatic epoxide groups of the glycidyl ether of the    polyol are reacted with the monofunctional amine-terminated    polyether.-   22) The process of paragraph 20, wherein the glycidyl ether of the    polyol comprises aliphatic epoxide groups, and wherein 20 to 100    percent of the aliphatic epoxide groups of the glycidyl ether of the    polyol are reacted with the monofunctional amine-terminated    polyether.-   23) The process of paragraphs 20 or 22, wherein the monofunctional    amine-terminated polyether is a polyetheramine.-   24) The process of paragraphs 20 to 23, wherein the monofunctional    amine-terminated polyether and the glycidyl ether of the polyol are    reacted under a temperature of from about 50° C. to about 150° C.-   25) A composition comprising:    -   a) a pigment component; and    -   b) an effective pigment-dispersing amount of a dispersant having        the structure:

-   -    in which R₁ may be any C₁-C₁₀₀ hydrocarbyl group; R₂ may be any        alkoxylated hydrocarbyl group defined by the structure:

in which R₃ is selected from the group consisting of: hydrogen, and anyC₁ to about C₂₄ hydrocarbyl group; X₁, X₂, X₃, X₄, X₅, and X₆ in eachoccurrence are independently selected from the group consisting of:hydrogen, methyl and ethyl, subject to the proviso that at least one ofthe two X groups that are attached to the same alkoxy unit are hydrogen,p, q, and r may each independently be any integer between zero and about100, including zero, subject to the proviso that at least one of p, q,and r is not zero; n is any integer between 1 and about 50; and s may beeither 0 or 1.

-   26) A composition according to paragraph 25, wherein the pigment    component is selected from the group consisting of phthalocyanine,    carbon black, titanium oxides, chromates, sulfides, iron oxides, azo    lakes, insoluble azo pigment, condensed azo pigments, chelate azo    pigments, monoazo pigments, monoarylide, B-naphthol, naphthol AS,    benzimidazolone, metal precipitated azo, disazo pigments, diarylide,    disazo condensation, diazopyrazoione, bisacetoacetarylide,    phthalocyanine pigments, perylenes, perylene, perinone pigments,    anthraquinone pigments, quinacridone pigments, dioxazine pigments,    thioindigo pigments, isoindolinone pigments, quinophthalone    pigments, base dye lakes, acid dye lakes, nitro pigments, nitroso    pigments, aniline black daylight fluorescent pigments, graphite    carbon, isoindoline, isoindolinon, indigoid, diketopyrrolopyrrole,    triarylcarbonium, metal complexes, pearl, liquid crystal pigments,    fluorescence, and functional derivatives of the above-mentioned    pigments.-   27) A composition according to paragraphs 25 or 26, further    comprising a solvent.-   28) A composition according to paragraph 27, wherein said solvent    comprises one or more organic solvents selected from the group    consisting of: polyhydric alcohols; glycols; diols; glycol esters;    glycol ethers; polyalkyl glycols; lower alkyl ethers of polyhydric    alcohols; alcohols having fewer than about 8 carbon atoms per    molecule; ketones; ethers; esters; and lactams.-   29) The composition according to paragraph 27, wherein the solvent    comprises water.-   30) The composition of paragraph 27, wherein the solvent is selected    from the group consisting of water; hexane; mineral spirits;    toluene; soy bean oil; castor oil; tall oil fatty acids; polyhydric    alcohols; glycols; diols; glycol esters; glycol ethers; polyalkyl    glycols; lower alkyl ethers of polyhydric alcohols; alcohols having    fewer than about 8 carbon atoms per molecule; ketones; ethers;    esters; lactams, ethylene glycol, propylene glycol; butanediol;    pentanediol; glycerol; propylene glycol laurate; polyethylene    glycol; ethylene glycol monomethyl ether, ethylene glycol mono-ethyl    ether; ethylene glycol mono-butyl ether; alcohols having fewer than    about 8 carbon atoms per molecule such as methanol, ethanol,    propanol, iso-propanol; acetone; dioxane; ethyl acetate, propyl    acetate, tertiary-butyl acetate, and 2-pyrrolidone.-   31) The composition of paragraphs 27 to 30, wherein the amount of    said solvent component present is any amount between about 10% and    99% by weight based on the total weight of said composition.-   32) The composition of paragraphs 27 to 31, wherein the amount of    said solvent component present is any amount between about 50% and    99% by weight based on the total weight of said composition.-   33) The composition of paragraphs 25 to 32, wherein the composition    comprises from about 1 weight % to about 80 weight % pigment, based    on the total weight of the composition.-   34) The composition of paragraphs 25 to 33, wherein the composition    comprises from about 1 weight % to about 40 weight % pigment, based    on the total weight of the composition.-   35) The composition of paragraphs 25 to 34, wherein the composition    comprises from about 2 weight % to about 10 weight % pigment, based    on the total weight of the composition.-   36) The use of the dispersant as described in paragraphs 25 to 35 in    an ink or coating composition.-   37) A dispersion comprising water, a pigment, and the dispersant as    described in paragraph 25.-   38) A dispersion comprising an organic solvent according to any    foregoing claim, a pigment, and a dispersant as described in    paragraph 25.-   39) A composition according to either paragraphs 25 to 38, wherein    said pigment comprises any pigment as stated in any foregoing claim.-   40) The use of a dispersant within the scope of the limitations    specified for the dispersant component of a composition according to    paragraphs 25 to 39 herein, in an ink which is either applied to or    intended to be applied to a substrate which comprises a material    selected from the group consisting of cellulose, any olefin polymer,    polyethers, polyvinylchloride, glass, polyamides, polyurethane,    metal composites, and the like.-   41) Any liquid ink composition which comprises a material falling    within the definition of the dispersant component of the composition    specified in paragraphs 25 to 40.-   42) An article comprising an ink or a coating,

wherein the ink further comprises:

-   -   a) a pigment component; and    -   b) an effective pigment-dispersing amount of a dispersant having        the structure:

-   -    in which R₁ may be any C₁-C₁₀₀ hydrocarbyl group; R₂ may be any        alkoxylated hydrocarbyl group defined by the structure:

in which R₃ is selected from the group consisting of: hydrogen, and anyC₁ to about C₂₄ hydrocarbyl group; X₁, X₂, X₃, X₄, X₅, and X₆ in eachoccurrence are independently selected from the group consisting of:hydrogen, methyl and ethyl, subject to the proviso that at least one ofthe two X groups that are attached to the same alkoxy unit are hydrogen,p, q, and r may each independently be any integer between zero and about100, including zero, subject to the proviso that at least one of p, q,and r is not zero; n is any integer between 1 and about 50; and s may beeither 0 or 1.

-   43) The article of paragraph 42, wherein the article is formed from    a material selected from the group consisting of metals, alloys,    composites, plastics, concrete, cast iron, wood, ceramic, paper,    film, foil, vinyl, textile, glass, and leather.-   44) A process for the formation of an ink or a coating composition    comprising:    -   a) reacting a monofunctional amine-terminated polyether and a        glycidyl ether of a polyol to form a dispersant; and    -   b) contacting the dispersant and a pigment to form a pigment        dispersion.-   45) The process of paragraph 44, wherein the glycidyl ether of the    polyol comprises aromatic epoxide groups, and wherein 20 to 90    percent of the aromatic epoxide groups of the glycidyl ether of the    polyol are reacted with the monofunctional amine-terminated    polyether.-   46) The process of paragraph 44, wherein the glycidyl ether of the    polyol comprises aliphatic epoxide groups, and wherein 20 to 100    percent of the aliphatic epoxide groups of the glycidyl ether of the    polyol are reacted with the monofunctional amine-terminated    polyether.-   47) The process of paragraphs 44 or 46, wherein the monofunctional    amine-terminated polyether is a polyetheramine.-   48) The process of paragraphs 44 to 47, wherein the monofunctional    amine-terminated polyether and the glycidyl ether of the polyol are    reacted under a temperature of from about 50° C. to about 150° C.-   49) A composition comprising:    -   a) a pigment component;    -   b) an effective pigment-dispersing amount of a dispersant having        the structure:

in which R₁ may be any C₁-C₁₀₀ hydrocarbyl group; R₂ may be anyalkoxylated hydrocarbyl group defined by the structure:

in which R₃ is selected from the group consisting of: hydrogen, and anyC₁ to about C₂₄ hydrocarbyl group; X₁, X₂, X₃, X₄, X₅, and X₆ in eachoccurrence are independently selected from the group consisting of:hydrogen, methyl and ethyl, subject to the proviso that at least one ofthe two X groups that are attached to the same alkoxy unit are hydrogen,p, q, and r may each independently be any integer between zero and about100, including zero, subject to the proviso that at least one of p, q,and r is not zero; n is any integer between 1 and about 50; and s may beeither 0 or 1; and

c) a grind resin.

-   50) The composition of paragraph 49, wherein the grind resin and the    dispersant are the same.-   51) The composition of paragraphs 49 or 50, wherein the grind resin    comprises:    -   a) a styrene, substituted-stryene monomer, or combinations        thereof and    -   b) a carboxylated monomer, wherein the carboxylated monomer is        selected from the group consisting of substituted or        unsubstituted acrylic acid, methacrylic acid, maleic acid, the        half esters of maleic acid, citriconic acid, itaconic acid, and        combinations thereof.-   52) The composition of paragraphs 49 to 51, wherein the grind resin    is a styrene acrylate.-   53) The composition of paragraphs 49 to 52, wherein the viscosity of    the composition is less than or equal to the viscosity of the    dispersant for all shear rates, and wherein the viscosity of the    composition is less than or equal to the viscosity of the grind    resin for all shear rates.-   54) The composition of paragraphs 49 to 53, wherein composition    comprises from about 0.1 weight % to about 40 weight % grind resin,    based on the weight of the pigment.-   55) The composition of paragraphs 49 to 54, wherein the pigment    component is selected from the group consisting of phthalocyanine,    carbon black, titanium oxides, chromates, sulfides, iron oxides, azo    lakes, insoluble azo pigment, condensed azo pigments, chelate azo    pigments, monoazo pigments, monoarylide, B-naphthol, naphthol AS,    benzimidazolone, metal precipitated azo, disazo pigments, diarylide,    disazo condensation, diazopyrazoione, bisacetoacetarylide,    phthalocyanine pigments, perylenes, perylene, perinone pigments,    anthraquinone pigments, quinacridone pigments, dioxazine pigments,    thioindigo pigments, isoindolinone pigments, quinophthalone    pigments, base dye lakes, acid dye lakes, nitro pigments, nitroso    pigments, aniline black daylight fluorescent pigments, graphite    carbon, isoindoline, isoindolinon, indigoid, diketopyrrolopyrrole,    triarylcarbonium, metal complexes, pearl, liquid crystal pigments,    fluorescence, and functional derivatives of the above-mentioned    pigments.-   56) The composition of paragraphs 49 to 55, wherein the composition    comprises from about 1 weight % to about 80 weight % pigment, based    on the total weight of the composition.-   57) The composition of paragraphs 49 to 56, wherein the composition    comprises from about 1 weight % to about 40 weight % pigment, based    on the total weight of the composition.-   58) The composition of paragraphs 49 to 57, wherein the composition    comprises from about 2 weight % to about 10 weight % pigment, based    on the total weight of the composition.-   59) The composition according to paragraphs 49 to 58 further    comprising a solvent.-   60) The composition of paragraph 59, wherein the solvent is selected    from the group consisting of water; hexane; mineral spirits;    toluene; soy bean oil; castor oil; tall oil fatty acids; polyhydric    alcohols; glycols; diols; glycol esters; glycol ethers; polyalkyl    glycols; lower alkyl ethers of polyhydric alcohols; alcohols having    fewer than about 8 carbon atoms per molecule; ketones; ethers;    esters; lactams, ethylene glycol, propylene glycol; butanediol,;    pentanediol; glycerol; propylene glycol laurate; polyethylene    glycol; ethylene glycol monomethyl ether, ethylene glycol mono-ethyl    ether; ethylene glycol mono-butyl ether; alcohols having fewer than    about 8 carbon atoms per molecule such as methanol, ethanol,    propanol, iso-propanol; acetone; dioxane; ethyl acetate, propyl    acetate, tertiary-butyl acetate, and 2-pyrrolidone.-   61) The composition of paragraphs 59 or 60, wherein the amount of    said solvent component present is any amount between about 10% and    99% by weight based on the total weight of said composition.-   62) The composition of paragraphs 49 to 61, wherein the amount of    said solvent component present is any amount between about 50% and    99% by weight based on the total weight of said composition.-   63) The use of the dispersant of paragraphs 49 to 62 in a coating    composition.-   64) An article comprising a coating,

wherein the coating further comprises:

-   -   a) a pigment component;    -   b) an effective pigment-dispersing amount of a dispersant having        the structure:

-   -    in which R₁ may be any C₁-C₁₀₀ hydrocarbyl group; R₂ may be any        alkoxylated hydrocarbyl group defined by the structure:

in which R₃ is selected from the group consisting of: hydrogen, and anyC₁ to about C₂₄ hydrocarbyl group; X₁, X₂, X₃, X₄, X₅, and X₆ in eachoccurrence are independently selected from the group consisting of:hydrogen, methyl and ethyl, subject to the proviso that at least one ofthe two X groups that are attached to the same alkoxy unit are hydrogen,p, q, and r may each independently be any integer between zero and about100, including zero, subject to the proviso that at least one of p, q,and r is not zero; n is any integer between 1 and about 50; and s may beeither 0 or 1; and

-   -   c) a grind resin.

-   65) The article of paragraph 64, wherein the article is formed from    a material selected from the group consisting of metals, alloys,    composites, plastics, concrete, cast iron, wood, ceramic, paper,    film, foil, vinyl, textile, glass, and leather.

-   66) A process for the formation of a coating composition comprising:    -   a) reacting a monofunctional amine-terminated polyether and a        glycidyl ether of a polyol to form a dispersant;    -   b) contacting the dispersant and a pigment to form a pigment        dispersion;    -   c) mixing the pigment dispersion and a grind resin.

-   67) The process of paragraph 66, wherein the glycidyl ether of the    polyol comprises aromatic epoxide groups, and wherein 20 to 90    percent of the aromatic epoxide groups of the glycidyl ether of the    polyol are reacted with the monofunctional amine-terminated    polyether.

-   68) The process of paragraph 66, wherein the glycidyl ether of the    polyol comprises aliphatic epoxide groups, and wherein 20 to 100    percent of the aliphatic epoxide groups of the glycidyl ether of the    polyol are reacted with the monofunctional amine-terminated    polyether.

-   69) The process of paragraphs 66 to 68, wherein the monofunctional    amine-terminated polyether is a polyetheramine.

-   70) The process of paragraphs 66 to 68, wherein the monofunctional    amine-terminated polyether and the glycidyl ether of the polyol are    reacted under a temperature of from about 50° C. to about 150° C.

-   71) A composition comprising:    -   a) a pigment component;    -   b) an effective pigment-dispersing amount of a dispersant having        the structure:

-   -    in which R₁ may be any C₁-C₁₀₀ hydrocarbyl group; R₂ may be any        alkoxylated hydrocarbyl group defined by the structure:

in which R₃ is selected from the group consisting of: hydrogen, and anyC₁ to about C₂₄ hydrocarbyl group; X₁, X₂, X₃, X₄, X₅, and X₆ in eachoccurrence are independently selected from the group consisting of:hydrogen, methyl and ethyl, subject to the proviso that at least one ofthe two X groups that are attached to the same alkoxy unit are hydrogen,p, q, and r may each independently be any integer between zero and about100, including zero, subject to the proviso that at least one of p, q,and r is not zero; n is any integer between 1 and about 50; and s may beeither 0 or 1; and

-   -   c) a grind resin.

-   72) The composition of paragraph 71, wherein the grind resin and the    dispersant are the same.

-   73) The composition of paragraphs 71 or 72, wherein the grind resin    comprises    -   a) a styrene, substituted-stryene monomer, or combinations        thereof and    -   b) a carboxylated monomer, wherein the carboxylated monomer is        selected from the group consisting of substituted or        unsubstituted acrylic acid, methacrylic acid, maleic acid, the        half esters of maleic acid, citriconic acid, itaconic acid, and        combinations thereof.

-   74) The composition of paragraphs 71 to 73, wherein the grind resin    is a styrene acrylate.

-   75) The composition of paragraphs 71 to 74, wherein the viscosity of    the composition is less than or equal to the viscosity of the    dispersant for all shear rates, and wherein the viscosity of the    composition is less than or equal to the viscosity of the grind    resin for all shear rates.

-   76) The composition of paragraphs 71 to 75, wherein composition    comprises from about 0.1 weight % to about 40 weight % grind resin,    based on the weight of the pigment.

-   77) The composition of paragraphs 71 to 76, wherein the pigment    component is selected from the group consisting of phthalocyanine,    carbon black, titanium oxides, chromates, sulfides, iron oxides, azo    lakes, insoluble azo pigment, condensed azo pigments, chelate azo    pigments, monoazo pigments, monoarylide, B-naphthol, naphthol AS,    benzimidazolone, metal precipitated azo, disazo pigments, diarylide,    disazo condensation, diazopyrazoione, bisacetoacetarylide,    phthalocyanine pigments, perylenes, perylene, perinone pigments,    anthraquinone pigments, quinacridone pigments, dioxazine pigments,    thioindigo pigments, isoindolinone pigments, quinophthalone    pigments, base dye lakes, acid dye lakes, nitro pigments, nitroso    pigments, aniline black daylight fluorescent pigments, graphite    carbon, isoindoline, isoindolinon, indigoid, diketopyrrolopyrrole,    triarylcarbonium, metal complexes, pearl, liquid crystal pigments,    fluorescence, and functional derivatives of the above-mentioned    pigments.

-   78) The composition of paragraphs 71 to 77, wherein the composition    comprises from about 1 weight % to about 80 weight % pigment, based    on the total weight of the composition.

-   79) The composition of paragraphs 71 to 78, wherein the composition    comprises from about 1 weight % to about 40 weight % pigment, based    on the total weight of the composition.

-   80) The composition of paragraphs 71 to 79, wherein the composition    comprises from about 2 weight % to about 10 weight % pigment, based    on the total weight of the composition.

-   81) The composition according to paragraphs 71 to 80 further    comprising a solvent.

-   82) The composition of paragraph 81, wherein the solvent is selected    from the group consisting of water; hexane; mineral spirits;    toluene; soy bean oil; castor oil; tall oil fatty acids; polyhydric    alcohols; glycols; diols; glycol esters; glycol ethers; polyalkyl    glycols; lower alkyl ethers of polyhydric alcohols; alcohols having    fewer than about 8 carbon atoms per molecule; ketones; ethers;    esters; lactams, ethylene glycol, propylene glycol; butanediol,;    pentanediol; glycerol; propylene glycol laurate; polyethylene    glycol; ethylene glycol monomethyl ether, ethylene glycol mono-ethyl    ether; ethylene glycol mono-butyl ether; alcohols having fewer than    about 8 carbon atoms per molecule such as methanol, ethanol,    propanol, iso-propanol; acetone; dioxane; ethyl acetate, propyl    acetate, tertiary-butyl acetate, and 2-pyrrolidone.

-   83) The composition of paragraphs 81 or 82, wherein the amount of    said solvent component present is any amount between about 10% and    99% by weight based on the total weight of said composition.

-   84) The composition of paragraphs 81 to 83, wherein the amount of    said solvent component present is any amount between about 50% and    99% by weight based on the total weight of said composition.

-   85) The use of the dispersant of paragraphs 71 to 84 in a coating    composition.

-   86) An article comprising a coating,

wherein the coating further comprises:

-   -   a) a pigment component;    -   b) an effective pigment-dispersing amount of a dispersant having        the structure:

-   -    in which R₁ may be any C₁-C₁₀₀ hydrocarbyl group; R₂ may be any        alkoxylated hydrocarbyl group defined by the structure:

in which R₃ is selected from the group consisting of: hydrogen, and anyC₁ to about C₂₄ hydrocarbyl group; X₁, X₂, X₃, X₄, X₅, and X₆ in eachoccurrence are independently selected from the group consisting of:hydrogen, methyl and ethyl, subject to the proviso that at least one ofthe two X groups that are attached to the same alkoxy unit are hydrogen,p, q, and r may each independently be any integer between zero and about100, including zero, subject to the proviso that at least one of p, q,and r is not zero; n is any integer between 1 and about 50; and s may beeither 0 or 1; and

-   -   c) a grind resin.

-   87) The article of paragraph 86, wherein the article is formed from    a material selected from the group consisting of metals, alloys,    composites, plastics, concrete, cast iron, wood, ceramic, paper,    film, foil, vinyl, textile, glass, and leather.

-   88) A process for the formation of a coating composition comprising:    -   a) reacting a monofunctional amine-terminated polyether and a        glycidyl ether of a polyol to form a dispersant;    -   b) contacting the dispersant and a pigment to form a pigment        dispersion;    -   c) mixing the pigment dispersion and a grind resin.

-   89) The process of paragraph 88, wherein the glycidyl ether of the    polyol comprises aromatic epoxide groups, and wherein 20 to 90    percent of the aromatic epoxide groups of the glycidyl ether of the    polyol are reacted with the monofunctional amine-terminated    polyether.

-   90) The process of paragraph 88, wherein the glycidyl ether of the    polyol comprises aliphatic epoxide groups, and wherein 20 to 100    percent of the aliphatic epoxide groups of the glycidyl ether of the    polyol are reacted with the monofunctional amine-terminated    polyether.

-   91) The process of paragraphs 88 to 90, wherein the monofunctional    amine-terminated polyether is a polyetheramine.

-   92) The process of paragraphs 88 to 90, wherein the monofunctional    amine-terminated polyether and the glycidyl ether of the polyol are    reacted under a temperature of from about 50° C. to about 150° C.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 illustrates the viscosity versus shear rate of variousformulations of ink premixes or coating premixes using a dispersantaccording to the present invention.

FIG. 2 illustrates the viscosity versus shear rate of carbon blackdispersion concentrates, wherein the dispersant comprises 25% carbonblack based on pigment.

FIG. 3 illustrates the viscosity versus shear rate of carbon blackdispersion concentrates, wherein the dispersant comprises 20% carbonblack or less based on pigment.

DETAILED DESCRIPTION

A component of a finished liquid ink composition or a pigmented coatingcomposition according to the present invention is a comb polymer, madein accordance herewith, which comb polymer serves to stabilize thepigment against agglomeration in the formulation.

A comb polymer suitable for use in an ink formulation or a pigmentedcoating composition according to one embodiment of the present inventionis formed by reacting a monofunctional, amine-terminated polyether witha glycidyl ether of a polyol. The product resulting from such a processmay be conveniently referred to as a polyetheralkanolamine. According toone preferred embodiment of the invention, the amine-terminatedpolyether (ATP) reactant is present in an amount sufficient to ensurethat the total number of reactive hydrogen atoms on the nitrogen atom ofthe amine(s) present is at least stoichiometrically equal to the amountof epoxide groups present in all glycidyl ethers of a polyols present.

In an embodiment, the present invention provides a process whichcomprises reacting a monofunctional, amine-terminated polyether (“ATP”)with a glycidyl ether of a polyol. A process according to an embodimentof the invention comprises reacting one or more epoxy resins (includingwithout limitation Bisphenol A and its derivatives and analogs) with anATP having a hydrophilic backbone (such as a polyethylene oxide (PEO)backbone) at elevated temperature, to afford a thermoplasticpolyetheralkanolamine having many hydrophilic branches. The polymermolecular weight and physical properties may be controlled by selectionof raw materials and ratio of the two starting materials.

A polyetheralkanolamine composition of the present invention may beprepared by reaction of a diglycidyl ether of Bisphenol A (or BisphenolF) with a mono-functional polyetheramine having a M_(w) of from about100 to about 12,000, alternatively from about 400 to about 10,000,alternatively from about 1,000 to about 7,000. The polyether (a.k.a.polyoxyalkylene) chain may be based on a polymer of ethylene oxide,propylene oxide, butylene oxide or any combination of these materials.The reaction may take place at any temperature between about 50° C. andabout 150° C., alternatively from about 80° C. to about 140° C.,alternatively from about 100° C. to about 130° C. Reaction times varyindependently, and may be any time between about 2 and about 10 hours.

In an embodiment, the general reaction scheme for the preparation of acomb polymer according to the present invention is:

in which an epoxy resin containing at least two epoxy functional endgroups is reacted with a primary amine. R₁ in the above reaction may beany aliphatic C₁ to C₁₀₀ hydrocarbyl group, alternatively any aliphaticC₆ to C₅₀ hydrocarbyl group, alternatively any C₁₀ to C₃₀ hydrocarbylgroup, alternatively an aromatic hydrocarbyl group; thus the epoxyreactant may be any epoxy resin of at least a functionality of two, andincludes without limitation the materials listed under the glycidylethers section of this specification.

In the above equation, n is any integer from 1 to about 50,alternatively from 1 to about 40, alternatively from about 2 to about30; R₂ may be any hydrocarbyl group which includes as a part of itsmolecular structure a portion containing at least two alkoxy groupslinked to one another, i.e., the group R₂ may be a group:

in which R₃ is any C₁ to about C₂₄ hydrocarbyl group; X₁, X₂, X₃, X₄,X₅, and X₆ in each occurrence are independently selected from the groupconsisting of: hydrogen, methyl and ethyl, subject to the proviso thatat least one of the two X groups that are attached to the same alkoxyunit are hydrogen, p, q, and r may each independently be any integerbetween zero and about 100, including zero, subject to the proviso thatat least one of p, q, and r is not zero.

The Amine Component

Such a group R₂ as specified above may be incorporated into a polymericdispersant of the invention by reaction of an amine having thestructure:

in which the variables are as defined above, with an epoxy resin havingat least di-functionality, as previously specified. Thus, the abovestructures include R₂ groups that include both random and block polymersand co-polymers of ethylene oxide, propylene oxide, and butylene oxide.According to one preferred form of the invention, the M_(w) of the aminereactant is any molecular weight from about 100 to about 12,000,alternatively from about 400 to about 10,000, alternatively from about1,000 to about 7,000. In cases where mixtures of such amines areemployed to produce a polymer provided herein, the preferred molecularweight will be an average molecular weight of all amines present, andthe production of alkoxylated amines probably results in the productionof a mixture of amines.

Thus, the mono-functional, amine-terminated polyethers used in thisinvention include mono-amines having a M_(w) of from about 100 to about12,000, alternatively from about 400 to about 10,000, alternatively fromabout 1,000 to about 7,000, which mono-amines include those marketed byHuntsman International LLC of Houston, Tex. under the trademarkSURFONAMINE®, as well as analogous compounds offered by other companiescomprising polyoxyalkylenated primary amines. Preferred amine-terminatedpolyethers have a M_(w) of from about 1,000 to about 7,000. While theseparticular materials are methoxy terminated, the amine-terminatedpolyethers used in practice of this invention may be capped with anyother groups in which the methyl group of the methoxy group is replacedwith a hydrogen or higher hydrocarbon such as ethyl, propyl, butyl,etc., including any hydrocarbyl substituent which comprises up to about18 carbons. In an embodiment, the amine termination is a primary aminegroup. Thus, mono-functional amine-terminated polyethers useful inaccordance with one embodiment of the present invention may have thegeneral structure:

in which R₁ and R₂ are each independently selected from the groupconsisting of: hydrogen and any C₁ to C₄ hydrocarbyl group; R₃ isindependently selected from the group consisting of: hydrogen, methyl,methoxy, ethoxy, and hydroxy; and wherein n is any integer in the rangeof from about 4 to about 100, alternatively form about 5 to about 90,alternatively from about 10 to about 70, and including mixtures ofisomers thereof. Such materials are available from HuntsmanInternational LLC of Houston, Tex.

The Glycidyl Ether Component

The glycidyl ethers of polyols useful in providing a compositionaccording to the present invention are generally known as “epoxy resins”which include various epoxy resins including conventional,commercially-available, epoxy resins. In addition, mixtures includingany two or more epoxy resins may be employed in any ratio of combinationwith one another to provide a mixture with which a primary amine as setforth herein may be reacted. In general, the epoxy resins can beglycidated resins, cycloaliphatic resins, epoxidized oils and so forth.The glycidated resins are frequently formed as the reaction product of aglycidyl ether, such as epichlorohydrin, and a bisphenol compound suchas bisphenol A. C₂-C₂₈, alternatively from about C₄ to about C₂₂,alternatively from about C₆ to about C₂₀ alkyl glycidyl ethers; C₂-C₂₈alternatively from about C₄ to about C₂₂, alternatively from about C₆ toabout C₂₀ alkyl-and-alkenyl-glycidyl esters; C₁-C₂₈, alternatively fromabout C₂ to about C₂₂, alternatively from about C₄ to about C₂₀ alkyl-,mono- and poly-phenol glycidyl ethers; polyglycidyl ethers ofpyrocatechol, resorcinol, hydroquinone, 4-4′-dihydroxydiphenyl methane(or bisphenol F), 4,4′-dihydroxy-3,3′-dimethyldiphenyl methane,4,4′-dihydroxydiphenyl dimethyl methane (or bisphenol A),4,4′-dihydroxy-3,3′-dimethyldiphenyl propane, 4,4′-dihydroxydiphenylsulfone, and tris (4-hydroxyphenyl)methane; polyglycidyl ethers ofNOVOLAC® resins; polyglycidyl ethers of diphenols obtained byesterifying ethers of di-phenols obtained by esterifying salts of anaromatic hydrocarboxylic acid with a dihaloalkane or dihalogen dialkylether; polyglycidyl ethers of polyphenols obtained by condensing phenolsand long chain halogen paraffins containing at least two halogen atoms;N,N′-diglycidyl-aniline;N,N′-dimethyl-N,N′-diglycidyl-4,4′-diaminodiphenyl methane;N,N,N′,N′-tetraglycidyl-4,4′-diaminodiphenyl methane;N,N′-diglycidyl-4-aminophenyl glycidyl ether; and combination thereof.Commercially-available epoxy resins that may be used in the practice ofthis invention include but are not limited to ARALDITE® GY6010 resin(Huntsman Advanced Materials LLC), ARALDITE® 6010 resin (HuntsmanAdvanced Materials LLC), EPON® 828 resin (Resolution Polymers), and DER®331 resin (the Dow Chemical Co.). Thus in an embodiment, the R₁ group ofa dispersant according to the present invention, may be a hydrocarbylresidue derived from a material as described above.

In an embodiment, the amine-terminated polyether and glycidyl ether of apolyol are present in such amounts that the amine group of the polyetheris able to be consumed by reacting with essentially all of the epoxidefunctionality of the glycidyl ether. Thus, during the reaction and in anembodiment, the amount of amine-terminated polyether isstoichiometrically equal to or greater than the amount of epoxide in theglycidyl ether of a polyol. The resulting product may have little, ifany, unreacted epoxide functionality left after the reaction. In anembodiment, from about 85 to about 100% of the epoxide groups of thestarting material are reacted. In an alternative embodiment, at least90% of the epoxide groups of the starting material are reacted. In astill further embodiment, at least 95% of the epoxide groups of thestarting material are reacted.

Depending on the starting amount used of a primary amine, it is possibleto form either a secondary or tertiary amine in the final product. It istherefore possible to form products which contain repeating units wherean ATP has reacted with two epoxide groups to form a tertiary amine.This result may be depicted by the following representative formula:

RNHCH₂CHOHCH₂—[—O-A-O—CH₂CHOHCH₂NRCH₂CHOHCH₂—O-]_(x)A-O—CH₂CHOHCH₂—NRH

in which R represents the capped polyether portion of the ATP; Arepresents a hydrocarbyl radical, such as the hydrocarbon portion ofhydrogenated bisphenol A; and x can vary from 0—if no tertiary aminesare present—to about 100, alternatively from 1 to about 80,alternatively from about 2 to about 50. Typically, this reaction canoccur at any temperature in the range of from about 50° C. to about 150°C., alternatively from about 80° C. to about 140° C., alternatively fromabout 100° C. to about 130° C., under ambient pressure.

The comb polymer component of the ink formulation or the pigmentedcoating composition according to the present invention typicallycomprises any amount between about 0.5 to about 25% by weight, based onthe total weight of all pigment solids present in the ink formulation orpigmented coating composition. According to an alternative embodiment,the comb polymer component of an ink formulation or pigmented coatingcomposition according to the present invention typically comprises anyamount between about 1% to about 10% by weight, based on the totalweight, of all pigment solids present in the ink formulation or thepigmented coating composition.

Pigment

The pigment component of the present invention is typically an insolublecolorant material, such as phthalocyanine. However, a wide variety oforganic and/or inorganic pigments may be present in an ink compositionor a pigmented coating composition according to the present invention.Representative examples of inorganic pigments are carbon black, titaniumoxides, chromates, sulfides, and iron oxides. Representative examples oforganic pigments are azo pigments (such as azo lakes, insoluble azopigment, condensed azo pigments, chelate azo pigments, monoazo pigments,including monoarylide, B-naphthol, naphthol AS, benzimidazolone, andmetal precipitated azo, as well as disazo pigments, including diarylide,disazo condensation, diazopyrazoione, and bisacetoacetarylide),polycyclic pigments (such as phthalocyanine pigments, perylenes,perylene, and perinone pigments, anthraquinone pigments, quinacridonepigments, dioxazine pigments, thioindigo pigments, isoindolinonepigments, and quinophthalone pigments), lake pigments (such as base dyelakes, and acid dye lakes), nitro pigments, nitroso pigments, andaniline black daylight fluorescent pigments. Other pigments may includeisoindoline, isoindolinon, indigoid, diketopyrrolopyrrole,triarylcarbonium, metal complexes, pearl, liquid crystal pigments,fluorescence, and functional derivatives of the above-mentionedpigments. Additionally, suitable pigments may include those that aredispersed in a water phase or those whose surfaces have been treatedwith a surfactant or a polymeric dispersing agent (such as graphitecarbon).

The amount of pigments present in an ink formulation or pigmentedcoating composition, according to the present invention, may varydepending upon the structure, and they may be present in any amountranging from about 1% to about 50%, alternatively from about 1 to about40, and in another embodiment, from about 2% to about 10% by weight,based on the total weight of ink or pigmented coating composition.

Carrier Medium (Solvent) Component

The ink composition or pigmented coating composition may include asolvent, which is sometimes referred to as the carrier medium. Thecarrier medium can be either aqueous or non-aqueous. When aqueous, thecarrier medium may be water or may comprise a mixture of water and atleast one organic solvent which is soluble in water to an appreciableextent. One preferred water-soluble organic solvent comprises one ormore polyhydric alcohols. In an embodiment, suitable polyhydric alcoholsinclude ethylene glycol, propylene glycol, and diols such as butanediol,pentanediol. Glycols and glycol esters are also useful, and includethose such as glycerol, propylene glycol laurate; polyalkyl glycols suchas polyethylene glycol; and lower alkyl ethers of polyhydric alcohols,such as ethylene glycol monomethyl ether, ethylene glycol mono-ethylether and ethylene glycol mono-butyl ether.

Other suitable water-soluble organic solvents include lower alcohols andall their isomers having fewer than about 8 carbon atoms per moleculesuch as methanol, ethanol, propanol, iso-propanol; ketones such asacetone; ethers such as dioxane; esters such as ethyl acetate, propylacetate, and lactams such as 2-pyrrolidone.

Still further suitable solvents include aliphatics such as hexane andmineral spirits; aromatics such as toluene; triglycerides such as soybean oil and castor oil; and fatty acids such as tall oil fatty acids.

The amount of solvent present in the ink formulation or the pigmentedcoating composition according to the invention is any amount in therange of between about 10% to about 99%, alternatively from about 10% toabout 90%, alternatively from about 50 to about 99%, alternatively fromabout 70% to about 99.8% based on total weight of the ink formulation orthe pigmented coating composition. Selection of the particular inkcomposition or the coating composition as being suitable for a givenfinal-use formulation depends on requirements of the specificapplication, such as desired surface tension and viscosity, the selectedpigment, drying time of the pigmented ink jet ink, type of paper ontowhich the ink will be printed, and proprieties of the final coating filmformation such as gloss, color strength, and transparency as isgenerally recognized or appreciated by a person of ordinary skill in theart.

Grind Resins

Pigments may be incorporated into a pigmented coating compositions bymixing a pigment dispersion and a grind resin. Suitable grind resinstypically comprise the polymerized residue of the styrene and/orsubstituted-styrene monomer and a carboxylated monomer. In anembodiment, the carboxylated monomer is selected from the groupconsisting of substituted or unsubstituted acrylic acid, methacrylicacid, maleic acid, the half esters of maleic acid, citriconic acid,itaconic acid, and combinations thereof. An example of a suitable grindresin is JONCRYL® 63 available from Johnson Polymer Sturtevant, Wis. Themolecular weight of JONCRYL® 63 is about 13,000. In an alternativeembodiment, the grind resin and the pigment dispersion are the same. Inthis embodiment, an additional amount of pigment dispersion acts as agrind resin.

The pigment dispersion and the grind resin may be mixed using mills suchas a ball mill, grind mill, continuous mill, or by any other means thateffectively integrates the pigment dispersion into the grind resin. Ingeneral, the pigmented dispersion and grind resin are effectivelyintegrated when the desired particle size of the pigment is achieved,the pigment is appropriately wetted by the grinding resin, and thepigment is uniformly dispersed throughout the grind resin.

In an embodiment, the grind resin is present in an amount from about 0.1percent to about 40 percent by weight based on the pigment. In analternative embodiment, the grind resin is present in an amount fromabout 1 percent to about 30 percent by weight based on the pigment. In astill further embodiment, the grind resin is present in an amount fromabout 2 percent to about 20 percent by weight based on the pigment. Inan embodiment, the size of the pigment is less than or equal to about 1micron after grinding, as measured by ultrasound technology usingDT-1200, which is manufactured by Dispersion Technologies Company.

Without wishing to be bound by the theory, Applicant believes that thereis a synergy between comb polymers of the present invention and grindresins, particularly wherein the grind resin is a styrene acrylate. Anembodiment of this synergistic effect is illustrated with reference toFIG. 2, wherein the viscosity of the blended composition is less than,or equal to, both the viscosity of the grind resin and the viscosity ofthe comb polymer.

Other Additives

An ink or coating pigment concentrate according to the present inventionmay be suitably prepared by combining the various components and mixingthem in a blender to homogenize, and grinding them in a bead mill. In anembodiment, the blender may be an ordinary kitchen blender. Optionally,a surfactant may be added to wet the pigment and modify the surfacetension of the ink to control penetration of the ink into the paper.Examples of suitable surfactants include nonionic, amphoteric, anionic,zwitterionic, and cationic surfactants, and those of ordinary skill inthis art are aware of the surfactants employed in this field. Otheradditives such as binders (resins), biocides, humectants, chelatingagents, viscosity modifiers, and defoamers may also be present in an inkcomposition according to the invention. Optionally, acrylic andnon-acrylic polymers may be added to improve properties such as waterfastness and smear resistance. These may be solvent based, emulsions,water soluble polymers, coalescing aids, anti-settling, thixotropes, orplasticizers.

The following examples are provided as illustrative examples of theinvention and shall not be construed as delimitive of the scope of thepresent invention whatsoever.

Preparation of Comb Polymers Preparative Example 1

200 grams (“g”) of molten SURFONAMINE® L-200 amine (0.2 equivalent)having a M_(w) of 2000 and a PO/EO ratio of about 2/42 was charged to a1-liter flask equipped with a mechanical stirrer and thermometer. Then37.6 g of ARALDITE® GY6010 diglycidyl ether of bisphenol A of equivalentweight 188 (0.2 equivalent) was added. The flask was heated to 120° C.for 7 hours and then the temperature of the liquid was lowered to 70° C.for 1 hour, after which the product was discharged. The resultingwater-soluble polyetheralkanolamine was a solid at 25° C. Its numberaverage molecular weight was about 4609 and weight average molecularweight was about 6155. Its surface tension was 51 dyne/cm at 100 ppm.

Preparative Example 2

To a small, wide mouth glass bottle was added SURFONAMINE® L-100 aminehaving a M_(w) of 1000, and PO/EO ratio of 3/19 (100 g, 0.2 moleequivalent) and EPON® 828 epoxy resin (30 g, 0.16 mole equivalent). Themixture was swirled to a homogeneous off-white solution and placed in a100° C. oven for five hours. The product at 25° C. was a soft, waxysemi-solid. The product was water soluble had a number average molecularweight of about 3413, and weight average molecular weight of about 4973.The surface tension of the product was about 48 dyne/cm at 100 ppm.

Preparative Example 3

300 g of molten SURFONAMINE L-300 amine (0.2 equivalent) having a M_(w)of 3000 and a PO/EO ratio of about 8/58 was placed in a 1-liter flaskequipped with a mechanical stirring, and thermometer. Then 37.6 g ofARALDITE® GY6010 (a diglycidyl ether of bisphenol A, having 188equivalent weight), 0.2 equivalent, was added. The flask was heated to120° C. for 7 hours and the temperature of the liquid was then loweredto 70° C. for about 1 hour, after which the product was discharged. Theresulting polyetheralkanolamine was a solid at room temperature andwater soluble. It had a number average molecular weight of about 4876and weight average molecular weight of about 6713.

Preparative Example 4

300 g of SURFONAMINE® L-207 amine (0.3 equivalent) having a M_(w) of2000 and a PO/EO ratio of about 10/31 was placed in a 1-liter flaskequipped with a mechanical stirring, and thermometer. Then 56.4 g ofARALDITE® GY6010 (a diglycidyl ether of bisphenol A, having 188equivalent weight), 0.3 equivalent, was added. The flask was heated to120° C. for 6 hours and the temperature of the liquid was then loweredto 70° C. for about 1 hour, after which the product was discharged. Theresulting polyetheralkanolamine was water soluble. It had a numberaverage molecular weight of about 3719 and weight average molecularweight of about 4657. The surface tension of the product was about 47dyne/cm at 100 ppm.

Preparative Example 5

To a small, wide mouth glass bottle was added SURFONAMINE® L-100 aminehaving a M_(w) of 1000, and PO/EO ratio of 3/19 (102.2 g, 0.2 moleequivalent), SURFONAMINE® B-100 amine having a molecular weight of 1000,and PO of 12.5 (61.3 g, 0.12 mole equivalent) and ARALDITE® GY6010 resin(61.5 g, 0.33 mole equivalent). The mixture was swirled to a homogeneousoff-white solution and placed in a 120° C. oven for eight hours. Theproduct was water soluble and had a number average molecular weight ofabout 3915, and weight average molecular weight of about 5996.

Preparative Example 6

300 g of SURFONAMINE® L-100 amine (0.6 equivalent) having a M_(w) of1000 and a PO/EO ratio of about 3/19 was placed in a 1-liter flaskequipped with a mechanical stirring, and thermometer. Then 200 g ofSURFONAMINE® B-200 amine (0.2 equivalent) having a molecular weight of2000, and a PO/E0 ratio of 29/6 was added. The flask was heated to 75°C. and 150.4 g of ARALDITE® GY6010 resin (a diglycidyl ether ofbisphenol A, having 188 equivalent weight), 0.8 equivalent, was added.The flask was heated to 120° C. for 6 hours and then the temperature ofthe liquid was lowered to 70° C., after which the product wasdischarged. The resulting polyetheralkanolamine was water soluble. Ithad a number average molecular weight of about 3115 and weight averagemolecular weight of about 6128.

Preparative Example 7

To a small, wide mouth glass bottle was added SURFONAMINE® L-100 aminehaving a M_(w) of 1000, and PO/EO ratio of 3/19 (100 g, 0.2 moleequivalent), and EPON® 862 (a Bisphenol F resin, 34.3 g, 0.2 moleequivalent). The mixture was swirled to a homogeneous off-white solutionand placed in a 120° C. oven for 10 hours. The final polymer was a solidat room temperature and was water soluble.

Preparative Example 8

To a small, wide mouth glass bottle was added SURFONAMINE® L-100 aminehaving a M_(w) of 1000, and PO/EO ratio of 3/19 (100 g, 0.2 moleequivalent), and EPONEX® 1510 resin (a hydrogenated Bisphenol A resin,45 g, 0.2 mole equivalent). The mixture was swirled to a homogeneousoff-white solution and placed in a 120° C. oven for 7 hours. The finalpolymer was a solid at room temperature and was water soluble.

Comparative Examples

These are materials currently offered to the market as dispersants foruse in inks and like formulations and suitable more or less, for variousend-use applications:

Example 1

Styrene-methacrylate copolymer (M_(w)˜12,000 and 30% styrene and 70%methacrylic acid by weight). This type of copolymer is mentioned in U.S.Pat. No. 4,597,794;

Example 2

Styrene-methacrylate copolymer (M_(w)˜12,000 and 50% styrene and 50%methacrylic acid by weight). This type of copolymer is mentioned in U.S.Pat. No. 4,597,794;

Example 3

Comb polymer of methacrylic acid/maleic anhydride/SURFONAMINE® B-30amine;

Example 4

SURFYNOL® CT-136 SURFACTANT, a surfactant for pigment grinding, suppliedby Air Products Company;

Example 5

DISPERBYK-190 dispersant, a pigment dispersant, supplied by BYK-Chemie,Inc;

Example 6

SURFONAMINE® L-100 amine, made and sold by Huntsman International LLC ofTexas;

Example 7

SURFONAMINE® L-200 amine, made and sold by Huntsman International LLC ofTexas;

Example 8

SURFONAMINE® L-300 amine, made and sold by Huntsman International LLC ofTexas;

Example 9

SURFONAMINE® L-207 amine, made and sold by Huntsman International LLC ofTexas;

Example 10

SURFYNOL® CT-324 surfactant, a surfactant for pigment grinding, suppliedby Air Products Company;

Premix (Pigment Concentrate) Formulations

The method of preparation of the following premix formulations involvesweighing the JONCRYL® 63 (binder), water, dispersant, into a beaker andmixed at low shear using a Silverson model L4RT-A mixer until they wereuniform. Then the pigment (carbon black) was added in three portions andmixed well to wet the particles between additions. After completeincorporation of the pigment, this composition (termed the premix) wasmixed for 10 minutes at high shear to begin the process of wetting andde-agglomeration of the pigment concentrates.

FORMULATION 1 Component Weight % Regal 660R (carbon black) 38.0Dispersant 2.0* JONCRYL ® 63 (30.5% of styrene acrylic 25.53 Resin fromS. C Johnson Polymer, binder) Byk ® 022 de-foamer, from BYK-Chemie 0.7Water 33.77 *Calculated based on 100% active

FORMULATION 2 Component Weight % Regal 660R (carbon black) 35.7Dispersant 2.0* JONCRYL ® 63 (30.5% of styrene acrylic 27.4 Resin fromS. C Johnson Polymer, binder) Byk ® 022 de-foamer, from BYK-Chemie 0.9Water 34.0 *Calculated based on 100% active

The viscosities of the premix were measured using a Bohlin Instruments,model CVO 120 Rheometer and Brookfield Viscometer.

Preparation of Pigment Concentrate (Dispersion)

A premix per the above was then milled on an Eiger Mini 100 horizontalmedia mill for 20 minutes to afford a dispersion.

Testing Procedures:

-   1) Tint strength (Sherwin Williams Superpaint Flat Interior Latex    Extra White to dispersion, 50 parts to 0.50 parts    respectively)—mixed on a Hauschild mixer for 1 minute at 1800 rpm.    Drawdowns of the tint mixture versus standard were made on Leneta    3NT-4 regular bond stock using a #20 wire wound rod.-   2) Viscosity was measured using a Brookfield Viscometer.-   3) Finished ink testing—color, transparency, gloss (all on prints    made with 360P 113 anilox on Leneta 3NT-3, film, and foil),    viscosity. The inks were made by using 30 parts letdown vehicle and    20 parts of dispersion. The vehicle contains: 65% ECO® 2177 acrylic    emulsion (from S. C. Johnson), 25% JONCRYL® 60 (34% solution of    JONCRYL® 678 styrene acrylic resin, and 10% water. The vehicle and    dispersion were weighed into Max 60 Hauschild containers and mixed 1    minute at 1800 rpm.

Comparative Viscosities of Pre-Mixes

FIG. 1 illustrates the viscosities of premix Formulation 1 usingdispersants from Preparation 1, Preparation 2, Preparation 3,Preparation 4 (present invention), and the viscosities of Example 1,Example 2, and Example 5.

Water Contact Angle Tests

A water contact angle was measured on a glass slide coated with a premixFormulation 1. The coated slide was dried at room temperature prior tothe contact angle measurement. A low contact angle indicates that thedispersant wets the pigment (carbon black) and thereby increasingdispersibility.

Contact Angle, degrees Untreated (no dispersant) 86.5 Example 5 55.6Preparation 1 25.9 Example 7 45.4

Viscosity Measurements

The viscosities of the dispersion of Formulation 2 containing adispersant were measured using a Brookfield Viscometer and listed below:

Dispersant Viscosity at 30 rpm, cps Preparation 1  60 (liquid)Preparation 4 240 (liquid) Example 4 Too high to measure (paste) Example10 Too high to measure (paste) Example 1 Too high to measure (paste)Example 2 Too high to measure (paste) Example 6 Too high to measure(paste) Example 7 Too high to measure (paste) Example 8 Too high tomeasure (paste) Example 9 Too high to measure (paste)

Ink Viscosities at Various Times

The following shows the pigment concentrate viscosities usingFormulation 2 after 24 hours.

RPM Untreated Example 4 Example 10 Preparation 1 Preparation 4Preparation 2 1.5 2227 2850 2887 197 213 2217 3 1320 1593 1628 171 1601005 6 819 971 1002 160 143 619 12 538 630 638 152 140 416 30 341 400398 147 135 293 60 250 297 290 143 130 204

Dispersion Tint Strength Observations

The following table compares the dispersion tint strength of variousdispersants using equivalent amounts of the dispersants in a pluralityof renditions of Formulation 2.

Additive Tint Strength Example 4 100.00 Example 10 98.27 Example 2104.71 Example 5 107.3 Preparative example 1 111.08

The following table compares the gloss 60° angle of carbon black ink ofvarious dispersants using formulation 1:

Additive Gloss Preparative example 1 43 Example 10 36.8 Example 4 38.5

Example 11

A blend containing 15% polyetheralkanol amine comb polymer (seePreparation 7 cited above), 11.25% water, 11.25% polyethylene glycol (MW400), and 62.5% JONCRYL® 63 was made by mixing at room temperature withan overhead mixer for 30 minutes. The blend (“Blend 1”) was first mixedwith water and defoamer and then carbon black was finally added slowly,according to the following formulation:

Component Weight % Regal ® 660R (carbon black) 38.5 Blend 1 (34% solid)19.25 Byk ® 022 (defoamer) 1.00 Water 41.25

In this example, Blend 1 was used at 15% active on pigment.

The premix was mixed at 3000 rpm for 3 minutes using a SpeedMixer™ andthen was milled at 3000 rpm for 3 minutes. The viscosity of the pigmentconcentrate was measured using a Bohlin Rheometer.

Example 12

In this example, Disperbyk 190 dispersant (40% solid), supplied by BYKChemie, was used at 20% active on pigment.

Component Weight % Regal ® 660R (carbon black) 38.5 Disperbyk 190 (40%solid) 19.25 Byk ® 022 (defoamer) 1.00 Water 41.25

The premix was mixed at 3000 rpm for 3 minutes using a SpeedMixer™ andthen was milled at 3000 rpm for 3 minutes. The viscosity of the pigmentconcentrate was measured using a Bohlin Rheometer.

Example 13

Component Weight % Regal ® 660R (carbon black) 38.5 Blend 1 (34% solid)28.31 Byk ® 022 (defoamer) 1.00 Water 32.19

The premix was mixed at 3000 rpm for 3 minutes using a SpeedMixer™ andthen was milled at 3000 rpm for 3 minutes. The viscosity of the pigmentconcentrate was measured using a Bohlin Rheometer.

In this example, the dosage of Blend 1 was 25% active on pigment.

Example 14

Component Weight % Regal ® 660R (carbon black) 38.5 JONCRYL ® 63 (30.5%solid) 31.56 Byk ® 022 (defoamer) 1.00 Water 28.94

The premix was mixed at 3000 rpm for 3 minutes using a SpeedMixer™ andthen was milled at 3000 rpm for 3 minutes. The viscosity of the pigmentconcentrate was measured using a Bohlin Rheometer.

In this example, JONCRYL®63 was used at 25% active on pigment.

Example 15

Component Weight % Regal ® 660R (carbon black) 38.5 Preparation 7 (100%solid) 9.625 Byk ® 022 (defoamer) 1.00 Water 50.875

The premix was mixed at 3000 rpm for 3 minutes using a SpeedMixer™ andthen was milled at 3000 rpm for 3 minutes. The viscosity of the pigmentconcentrate was measured using a Bohlin Rheometer.

In this example, Preparation 7 above was used at 25% active on pigment.

Example 16

Component Weight % Regal ® 660R (carbon black) 38.5 Preparation 7 (100%solid) 7.7 Byk ® 022 1.00 Water 54.8

The premix was mixed at 3000 rpm for 3 minutes using a SpeedMixer™ andthen was milled at 3000 rpm for 3 minutes. The viscosity of the pigmentconcentrate was measured using a Bohlin Rheometer.

In this example, Preparation 7 above was used at 20% active on pigment.

Example 17

Component Weight % Regal ® 660R (carbon black) 38.5 EXP 8451-30-2 (37.6%solid) 10.24 Byk ® 022 1.00 Water 50.26

In Example 17, 24% Preparation 7 above, 18% water, 18% polyethyleneglycol (M_(w) of 400), and 40% JONCRYL®HPD 96 from Johnson Polymer wereblended together to form Blend 2. The dosage of Blend 2 was 10% activeon pigment Blend 2 was made at room temperature with an overhead mixerfor 30 minutes. The premix was mixed at 3000 rpm for 3 minutes using aSpeedMixer™ and then was milled at 3000 rpm for 3 minutes. The viscosityof the pigment concentrate was measured using a Bohlin Rheometer.

FIGS. 1 and 2 compare the viscosities of various dispersants in carbonblack dispersions.

Consideration must be given to the fact that although this invention hasbeen described and disclosed in relation to certain preferredembodiments, obvious equivalent modifications and alterations thereofwill become apparent to one of ordinary skill in this art upon readingand understanding this specification and the claims appended hereto. Thepresent disclosure includes the subject matter defined by anycombination of any one of the various claims appended hereto with anyone or more of the remaining claims, including the incorporation of thefeatures and/or limitations of any dependent claim, singly or incombination with features and/or limitations of any one or more of theother dependent claims, with features and/or limitations of any one ormore of the independent claims, with the remaining dependent claims intheir original text being read and applied to any independent claim somodified. This also includes combination of the features and/orlimitations of one or more of the independent claims with the featuresand/or limitations of another independent claim to arrive at a modifiedindependent claim, with the remaining dependent claims in their originaltext being read and applied to any independent claim so modified.Accordingly, the presently disclosed invention is intended to cover allsuch modifications and alterations, and is limited only by the scope ofthe claims which follow, in view of the foregoing and other contents ofthis specification.

1) A composition comprising: a) a pigment component; b) an effectivepigment-dispersing amount of a dispersant having the structure:

in which R₁ may be any C₁-C₁₀₀ hydrocarbyl group; R₂ may be anyalkoxylated hydrocarbyl group defined by the structure:

in which R₃ is selected from the group consisting of: hydrogen, and anyC₁ to about C₂₄ hydrocarbyl group; X₁, X₂, X₃, X₄, X₅, and X₆ in eachoccurrence are independently selected from the group consisting of:hydrogen, methyl and ethyl, subject to the proviso that at least one ofthe two X groups that are attached to the same alkoxy unit are hydrogen,p, q, and r may each independently be any integer between zero and about100, including zero, subject to the proviso that at least one of p, q,and r is not zero; n is any integer between 1 and about 50; and s may beeither 0 or 1; and c) a grind resin. 2) The composition of claim 1,wherein the grind resin and the dispersant are the same. 3) Thecomposition of claim 1, wherein the grind resin comprises a) a styrene,substituted-stryene monomer, or combinations thereof and b) acarboxylated monomer, wherein the carboxylated monomer is selected fromthe group consisting of substituted or unsubstituted acrylic acid,methacrylic acid, maleic acid, the half esters of maleic acid,citriconic acid, itaconic acid, and combinations thereof. 4) Thecomposition of claim 1, wherein the grind resin is a styrene acrylate.5) The composition of claim 1, wherein the viscosity of the compositionis less than or equal to the viscosity of the dispersant for all shearrates, and wherein the viscosity of the composition is less than orequal to the viscosity of the grind resin for all shear rates. 6) Thecomposition of claim 1, wherein composition comprises from about 0.1weight % to about 40 weight % grind resin, based on the weight of thepigment. 7) The composition of claim 1 wherein the pigment component isselected from the group consisting of phthalocyanine, carbon black,titanium oxides, chromates, sulfides, iron oxides, azo lakes, insolubleazo pigment, condensed azo pigments, chelate azo pigments, monoazopigments, monoarylide, B-naphthol, naphthol AS, benzimidazolone, metalprecipitated azo, disazo pigments, diarylide, disazo condensation,diazopyrazoione, bisacetoacetarylide, phthalocyanine pigments,perylenes, perylene, perinone pigments, anthraquinone pigments,quinacridone pigments, dioxazine pigments, thioindigo pigments,isoindolinone pigments, quinophthalone pigments, base dye lakes, aciddye lakes, nitro pigments, nitroso pigments, aniline black daylightfluorescent pigments, graphite carbon, isoindoline, isoindolinon,indigoid, diketopyrrolopyrrole, triarylcarbonium, metal complexes,pearl, liquid crystal pigments, fluorescence, and functional derivativesof the above-mentioned pigments. 8) The composition of claim 1, whereinthe composition comprises from about 1 weight % to about 80 weight %pigment, based on the total weight of the composition. 9) Thecomposition of claim 8, wherein the composition comprises from about 1weight % to about 40 weight % pigment, based on the total weight of thecomposition. 10) The composition of claim 9, wherein the compositioncomprises from about 2 weight % to about 10 weight % pigment, based onthe total weight of the composition. 11) The composition according toclaim 1 further comprising a solvent. 12) The composition of claim 11,wherein the solvent is selected from the group consisting of water;hexane; mineral spirits; toluene; soy bean oil; castor oil; tall oilfatty acids; polyhydric alcohols; glycols; diols; glycol esters; glycolethers; polyalkyl glycols; lower alkyl ethers of polyhydric alcohols;alcohols having fewer than about 8 carbon atoms per molecule; ketones;ethers; esters; lactams, ethylene glycol, propylene glycol; butanediol;pentanediol; glycerol; propylene glycol laurate; polyethylene glycol;ethylene glycol monomethyl ether, ethylene glycol mono-ethyl ether;ethylene glycol mono-butyl ether; alcohols having fewer than about 8carbon atoms per molecule such as methanol, ethanol, propanol,iso-propanol; acetone; dioxane; ethyl acetate, propyl acetate,tertiary-butyl acetate, and 2-pyrrolidone. 13) The composition of claim12, wherein the amount of said solvent component present is any amountbetween about 10% and 99% by weight based on the total weight of saidcomposition. 14) The composition of claim 13, wherein the amount of saidsolvent component present is any amount between about 50% and 99% byweight based on the total weight of said composition. 15) The use of thedispersant of claim 1 in a coating composition. 16) (canceled) 17)(canceled) 18) A process for the formation of a coating compositioncomprising: a) reacting a monofunctional amine-terminated polyether anda glycidyl ether of a polyol to form a dispersant; b) contacting thedispersant and a pigment to form a pigment dispersion; c) mixing thepigment dispersion and a grind resin. 19) The process of claim 18,wherein the glycidyl ether of the polyol comprises aromatic epoxidegroups, and wherein 20 to 90 percent of the aromatic epoxide groups ofthe glycidyl ether of the polyol are reacted with the monofunctionalamine-terminated polyether. 20) The process of claim 18, wherein theglycidyl ether of the polyol comprises aliphic epoxide groups, andwherein 20 to 100 percent of the aliphatic epoxide groups of theglycidyl ether of the polyol are reacted with the monofunctionalamine-terminated polyether. 21) The process of claim 18, wherein themonofunctional amine-terminated polyether is a polyetheramine. 22) Theprocess of claim 18, wherein the monofunctional amine-terminatedpolyether and the glycidyl ether of the polyol are reacted under atemperature of from about 50° C. to about 150° C.
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